Fantasy Fest in Key West - Schedule of Events

Key West, FL -

Here’s the schedule of events…so far. Please keep checking back for updates, we’ll do our best to keep you informed. If in doubt, email us at events@tripsmarter.com and we’ll find out what you don't know…or something like that!

This year, Key West celebrates 30 years of Fantasy Fest with even more fantastical fun shared as usual by more than 70,000 costumed partygoers from all over the world. This year's theme is "Villains, Vixens, and Vampires."

Fantasy Fest 2009 promises to have it all! Parades, costume contests, street parties, and much more! Can't wait for Fantasy Fest 2009? Check out our Fantasy Fest Photo Gallery for tons of great photos from previous years!

Friday, October 23rd

Royal Coronation Ball
Meet Key West’s Royal Family and vote for the King and Queen of Fantasy Fest 2009; a benefit for AIDS Help, Inc.;TBA

Goombay
Tastes, sights and sounds of the Caribbean in Bahama Village, located at Duval and Petronia streets. The lively street party continues Saturday! Noon - midnight; FREE

Saturday, October 24

Goombay
The party continues in Bahama Village! Noon - midnight; FREE

Vampire's Ball sponsored by Albertson's
All vampires sink your teeth into this tropical Transylvania! While mingling amongst the neonates and mortals visit The Haunting of Fort Taylor 2009! Fantasy, mystery, and fun await you on this enchanted evening! Music, dancing, food, and drinks sponsored by Albertson's. Costume contest with fabulous prizes! Haunting of Fort Taylor opens at 8pm. The best Party from Ghost to Ghost!; FT. Zachary Taylor at the end of Southard; 7-9 p.m.

Monday, October 26

Pinking of You!
Looking for an outrageous costume idea for Fantasy Fest? Want to partake in a wildly fun event where you can mingle with local celebrities and bid on one-of-a-kind bra inspired creations? The Third Annual “Pinking of You” Decorated Bra Auction promises to be a great time for a great cause. Local artists transform bras into works of art which are then modeled during a live auction to the highest bidder. You never know what you might see—drag queens sporting brassieres made of money or dames donning feathered bra purses! All money raised will be donated to WomanKind, inc. to provide breast cancer education and early detection through clinical breast exams.; 6pm; La Te Da 1125 Duval St.

Dungeons and Dragons
A leather fetish party that’s definitely not for the timid or shy!; 801 Bourbon Bar;(305)293-9800;9 pm

Tuesday, October 27

Reddy Ice Fantasy Facade Competition
Festively decorated homes and businesses compete for cold cash! To enter, call 305-296-5334

Finnegan's Wake Green Party
Come celebrate the ultimate Irish party! Wear your green and receive NO COVER; 8 pm; 320 Grinnell St.; 305-293-0222

Party in Plaid
Swing into Fantasy Fest at legendary Capt. Tony's Saloon! Explore your fantasies in naughty or nice plaid attire. Meet new friends, enjoy live music and rum specials all night long. FREE. www.capttonyssaloon.com;428 Greene St.; 9pm.

Free Official Fantasy Fest Poster Signing Party
Meet-n-greet the award-winning artist of this year's poster. Get up close and personal while having a lively libation; Crowne Plaza La Concha Hotel; 430 Duval St.; 5 pm; posters for sale.

27th Annual Headdress Ball
Elaborate Headdress Contest, Show featuring live entertainment, and Party. This year’s theme is Heroes and Villains with Prizes for Best Headdress; (costumes not judged) $1,000 first; $300 second; $200 third; Reserved Tables VIP for 4- $320 or $270; standing/ open seating in rear $40. Southernmost Hotel, 1319 Duval Street, Seating begins 7 pm, 8 pm Curtain. www.keystix.com or 305-296-1520.

Wednesday, October 28

Celebrity Look-a-like Contest
Do people always tell you that you remind them of someone famous? Well then this is your event! Imitators of the famous and fabled vie for cash and prizes; Crowne Plaza La Concha Hotel; 430 Duval St.; Contestant sign up 8 pm; FREE to watch; FREE to enter..

Homemade Bikini Contest & Beach Party
Hog's Breath Saloon proudly presents the 22nd Annual Fantasy Fest Homemade Bikini Contest and Beach Party. Details of the contest are at www.hogsbreath.com; 400 Front St.; 305- 296-4222; 10 pm.

WKEY Pet Masquerade & Parade
A magical carousel of frisky pets and playful owners delightfully disguised and ready to frolic for fame and fortune; Registration for competition is at 4:30 pm; FREE to watch; $25 to enter; benefits Lower Keys Friends of Animals; Casa Marina Resort & Beach Club; 1500 Reynolds St.

Fogarty's Red Night
Fogarty's 8th Annual Red Party! Don't miss this often imitated, but never duplicated party; Costume Contest; Door Prizes; Live DJ; 227 Duval St.;305-294-7525.

Thursday, October 29

Pretenders in Paradise
The legendary costume competition with $10,000 in cash and prizes! Combining extraordinary creative genius and performing energy, this year's event promises to be eye popping entertainment; Pier House Resort & Caribbean Spa. www.pierhouse.com; 8pm.

Monster's Ball
Sea serpents, mermaids and other bizarre creatures of the deep! What lurks below and who's dancing on the reef? Dive into this annual costume party and explore some surreal fantasies and some-too-real fantasies that should perhaps remain submerged! Green Parrot Bar; 601 Whitehead St.; 505-294-6133; 10 pm; FREE

Cowboy Bill's 3rd Annual Git-R-Wet T-Shirt Contest
Catch the hottest ladies competing for $1,500 in cash prizes in this over-the- top competition. Contestants model the finest in creative cotton wet t- shirt apparel. DJ Bill Hoebee MC's all the wild festivities. See the action live at www.CowboyBillsKW.com 610 1/2 Duval St.; 10 pm; 295-8219; VIP seating available, Door Charge.

Sloppy Joe's 26th Annual Toga Party
"Still The Best Ancient Roman Party In Town!" To enter contest, contestants must be dressed in toga and are encouraged to dress in Fantasy Fest theme “Pirates, Pundits and Political Party Animals.” Three divisions: Groups/Couples $500 first place; Men’s $250 first place; and Women’s first place $250. Free to enter contest; registration at 8:00 pm and contest begins at 9:30 pm; Door charge; www.sloppyjoes.com; 201 Duval St.

Pajama and Lingerie Party
The hottest Playboy model in the world Kristy Morgan from the reality TV show "Tila Tequila" encourages you to dress sexy for this skimpy affair. Enter the $700 Hugh Hefner and Marilyn Monroe look-a-like contest, plus enjoy guest D.J.'s live. This event is guaranteed to sell out.;Purchase advance VIP tickets online at www.keystix.com; Mangoes; 700 Duval Street; 305-304-1188; 10 pm.

Dante's 3rd Annual "Halos & Horns" Pool Party & Wet T-Shirt Contest
Free Body Painting, Super Food and Drink specials, Great Give-aways, Live Music with Caffeine Carl & The Buzz, our unique stage in the center of the POOL, and lot's of $$$$ to give away; Whether you wear the halo of an ANGEL or prefer devilish Horns, come strut your STUFF @DANTE'S 3rd annual HALOS & HORNS pool party and wet t-shirt contest. The Party starts at Noon and goes till 6:00, Pole Dancing starts at 4:30, @ Dante's Restaurant & Raw Bar, 951 Caroline St, next to the Ferry Terminal; Call 305-293-5123 for more details or to sign up for the contest!

Friday, October 30

Pimp and Ho Party
America's #1 movie star, Ron Jeremy, invites you to come fulfill your fantasy at this exotic dance party. Enter the $700 Mr. Pimp and Ms. Ho costume contest, plus enjoy guest D.J.'s live. This event is guaranteed to sell out. Purchase advance VIP tickets online atwww.keystix.com; Redfish Bluefish; 407 Front Street; 305-304-1188; 10 pm.

Heaven & Hell Costume Contest
All Angels and Demons are hereby summoned to enter Heaven or Hell’s Gates at Southernmost Hotel’s Annual Costume Contest Friday, October 30th from 4-6 pm, a pre-event to the half-way party of the Masquarade March. Wander through the pearly gates and step into the realms of Heaven or Hell at the Southernmost Hotel where all is relaxing and peaceful, or is it?

9th Annual Living Art Airbrush Expo
Contestants will use the human form as a living canvas for artistic expression in competition for more than $1,500; drink specials and live entertainment; Sunset Pier at Ocean Key Resort; Painting and Partying Start at Sunset; judging begins at 9 pm; 305-295-7045.

Fairvilla Megastore Masquerade March
Join the crowd as they parade through Old Town with music and noisemakers; thirst quenchers provided at selected guesthouses. Begins at the Key West Cemetery Frances Street entrance; revelers can join the mad march anywhere along the two routes; 5pm; All welcome; sponsored by Key West's costume headquarters - Fairvilla Megastore. www.fairvilla.com.

Rum Barrel's 3rd Annual Pirate Bash
Dress and DRINK LIKE A PIRATE at the Rum Barrel! Key West’s resident pirate and rum experts --- Pirate Soul Museum and Rum Barrel Restaurant & Bar --- team up to throw the most outrageous Pirates Bash in the world! More than $1500 in cash prizes for the best pirate and wench costumes, great music on the rooftop stage, and awesome rum specials. More info at RumBarrel.com or (305) 292-7862. Piratical inspiration at PirateSoul.com.; 9pm.

Annual Street Fair
Duval Street's mile-long eater-tainment extravaganza features arts and crafts, food vendors, lively libations and costumed frivolity; 12 pm - 10 pm; Friday, October 30.

801 Bourbon Bar Tea Dance
Plenty of sugar and spice at this tea in the street party; Live DJ, cool drinks, dancers, drag queens and celebrities; 305-293-9800; 801 Duval St.; 1 pm; FREE.

Fetish and Fantasy Party at the Island House for Men
"Dressed to Thrill" costume judging & party for men co-sponsored by the Key West Wreckers at Island House. Imagine a costume party in your favorite dungeon. Win cash and prizes for best costume in each of three categories: 1 - Leather, Uniform or Rubber; 2 - Fetish; 3 - Best use of this year’s Fantasy Fest theme Villains, Vixens and Vampires. Judging at 9:30. Party follows in the special dungeon. Clothes check provided. Clothing optional. Adults only. Men only.

Big Uns 2nd Annual Costume Extravaganza
Join us at Key West's premiere entertainment complex for the most outrageous costume party. Come and compete for the title of Vilest Villain, Voluptuous Vixen and Vampiest Vampire. $1000.00 will be awarded in each category. Enjoy drink specials, party favors and live entertainment. You don't want to miss this event. 305-292-0486; 218 Duval St.; 9pm-1am.

Saturday, October 31

Captain Morgan Fantasy Fest Parade
Join 70,000 exuberant partygoers as this year's parade rolls down Duval Street. Featuring glittering floats, marching bands and dancing groups, it doesn't get any wilder than this! Parade route includes Whitehead, Front and Duval Streets; 7 pm. www.captainmorgan.com

Bourbon Street Pub Tea Dance and Balcony Brouhaha
Brace yourselves for one of Fantasy Fest's most outrageous daytime events! Bourbon St. Pub helps you to relive the glory-days of Key West's notoriously remembered "Tea In the Street." With Duval St. shut down, prepare for flying drag queens, hot male dancers, and in true Bourbon St. fashion--- FANTASY FEST BEADS!!! Live DJ, satellite bars and local celebs! Street level standing room always available at no charge. VIP Balcony Brouhaha tickets can be pre-purchased at The New Orleans House or by calling (305) 293-9800. Balcony tickets are guaranteed to sell out! 11am-5pm; Bourbon St. Pub Complex

Duval Street Promenade
Sassy entertainers, enticing food and spirited libations tempt costumed merrymakers as they party from the Gulf to the Atlantic; Noon - 10:30 pm; FREE.

Sunday, November 1

"The Fat Lady Sings" Tea Dance
As the saying goes, "It ain't over 'til the fat lady sings." Everyone will be at La Te Da from 4pm to 9pm for the last Official Event of Fantasy Fest 2009. DJ Junior provides the music for the very last hoorah. La Te Da Hotel, Restaurant, Cabaret and Bars; 1125 Duval Street; (305)296-6706; www.LaTeDa.com; $5 admission.

Official Big Pecker Wine Tasting
Stop by MM 28.5 on your way out of town for a free wine tasting of Big Pecker Wine; the Official Wine Sponsor of Fantasy Fest 2009; 11 am to 11 pm; Parrotdise Waterfront Bar & Grille; 183 Barry Ave., Little Torch Key; 305- 872-9989; www.parrotdisewaterfront.com

Children's Day
A family event featuring food, games, arts and crafts and a costume contest for children. Bayview Park at Truman Ave. and Eisenhower Dr.; 305-292-8912